Benzoyl isothiocyanate → HCID 59621286, compound

HRID 1842142Notes

Reaction equation

HRID 1842142 reaction equation
[NH2:1][C@@:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:7][CH2:6][CH:5]([O:8][CH3:9])[CH2:4][C@H:3]1[CH2:10][OH:11].[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:19]([NH:27][C:28]([NH:1][C@@:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:7][CH2:6][CH:5]([O:8][CH3:9])[CH2:4][C@H:3]1[CH2:10][OH:11])=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 59621297HCID 59621297, compound

Product 1

HCID 59621286HCID 59621286, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-[(1R*,2S*)-2-Amino-2-(2-fluorophenyl)-5-methoxycyclohexyl]methanol obtained in Preparation Example 59-(6) (5.49 g) was dissolved in dichloromethane (22 mL). Then, benzoyl isothiocyanate (3.04 mL, specific gravity: 1.21 g/cm3) was added and the mixture was stirred at room temperature for 16 hours and 30 minutes. The reaction solution was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain the title compound (7.16 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-58475d0fd3a04b47a1e6f9e8ba8f93e4
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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