# US 7,411,096 B2 · Process for producing optically active phosphorus heterocyclic dimer

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- Number: US 7,411,096 B2
- Document ID: US7411096B2
- Status: Granted
- Kind: B2
- Application number: 10/564,985
- Filed: 2004-07-27
- Published: 2006-09-21
- Granted: 2008-08-12
- Earliest claimed: 2003-07-28
- Assignees: Nippon Chemical Industrial Co., Ltd.
- Inventors: Nobuhiko Oohara; Tsuneo Imamoto
- Web page: https://patentgrep.com/patent/US7411096B2

## CPC

- C07F 9/65683: {the ring phosphorus atom being part of a phosphine}
- C07F 9/65685: {the ring phosphorus atom being part of a phosphine oxide or thioxide}
- C07F 15/008: {without a metal-carbon linkage}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

The present invention provides a process for producing an optically active phosphorus heterocyclic dimer including reacting, in the presence of a base, primary phosphine represented by formula (1) R—PH2 (1) is reacted with a compound represented by formula (2) Y—CnH2n—Y (2) in the presence of a base; the product is reacted with boron trihydride, oxygen, or sulfur to obtain a phosphorus heterocyclic compound represented by formula (3): the resultant compound is dimerized to produce a phosphorus heterocyclic dimer represented by formula (4): and then oxygen, sulfur, or borane is removed from the resultant phosphorus heterocyclic dimer to obtain an optically active phosphorus heterocyclic dimer represented by formula (5):

## Claims

### Claim 1

A process for producing a phosphorus heterocyclic dimer according to formula (5) comprising the steps of:
reacting, in the presence of a n-butyl lithium, primary phosphine represented by formula (1):
R—PH2 (1)
(wherein R represents a linear or a branched alkyl group having 2 to 20 carbon atoms or a cyclic alkyl group having 3 to 20 carbon atoms) with a compound represented by formula (2):
Y—CnH2n—Y (2)
(wherein Y represents a halogen atom or a leaving group selected from -OTs, -OTf, and -OMs, and n represents a number of 3 to 6);
reacting a product, which was obtained by said step of reacting primary phosphine represented by formula (1) with a compound represented by formula (2), with boron trihydride, oxygen, or sulfur to obtain a phosphorus heterocyclic compound represented by formula (3):
(wherein R represents a linear or a branched alkyl group having 2 to 20 carbon atoms or a cyclic alkyl group having 3 to 20 carbon atoms, n equals 1, X represents a boron trihydride group, an oxygen atom, or a sulfur atom, and ═══ represents a single bond when X is a boron trihydride group or a double bond when X is an oxygen atom or sulfur atom);
dimerizing the phosphorus heterocyclic compound represented by formula (3) to produce a phosphorus heterocyclic dimer represented by formula (4):
(wherein R represents a linear or a branched alkyl group having 2 to 20 carbon atoms or a cyclic alkyl group having 3 to 20 carbon atoms, n equals 1, X represents a boron trihydride group, an oxygen atom, or a sulfur atom); and
removing oxygen, sulfur, or borane from the phosphorus heterocyclic dimer represented by formula (4) to obtain an optically active phosphorus heterocyclic dimer represented by formula (5):
wherein R represents a linear or a branched alkyl group having 2 to 20 carbon atoms or a cyclic alkyl group having 3 to 20 carbon atoms, n equals 1); and
wherein the compound represented by formula (2) is 1,3-dichloropropane.