Bromotrimethylsilane → HCID 86739192, compound

HRID 2295991Notes

Reaction equation

HRID 2295991 reaction equation
C([O:3][P:4]([CH2:16][C:17]([N:19]1[C@H:28]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1)=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])C.Br[Si](C)(C)C>ClCCl>[OH:5][P:4]([CH2:16][C:17]([N:19]1[C@H:28]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1)=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86739193HCID 86739193, compound

Product 1

HCID 86739192HCID 86739192, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-1,2,3,4-tetrahydro-2-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-3-isoquinolinecarboxylic acid, phenylmethyl ester (1.07 g., 2.0 mmole) from Example 1(e) in dry dichloromethane (5 ml.) is treated with bromotrimethylsilane (0.4 ml., 3 mmole) and stirred at room temperature under argon for 16 hours. The mixture is evaporated to dryness and the residue is partitioned between ethyl acetate-water. The ethyl acetate phase is washed with saturated sodium chloride solution, dried (Na2SO4) and evaporated to give (S)-1,2,3,4-tetrahydro-2-[[hydroxy(4-phenylbutyl)phosphinyl]-acetyl]-3-isoquinolinecarboxylic acid, phenylmethyl ester.

Workup

  1. customThe mixture is evaporated to dryness
  2. customthe residue is partitioned between ethyl acetate-water
  3. washThe ethyl acetate phase is washed with saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-eef7df25bfa74be08067590e1ae7744c
Source dataset
uspto-grants-1984_01
Patent number
US04427665

Reaction notes

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