Water → HCID 86652374, compound

HRID 2063707Notes

Reaction equation

HRID 2063707 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[C@H:11]([CH2:21]C#N)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].[OH2:29]>ClCCl>[CH3:24][S:25]([O:27][CH2:21][C@@H:11]1[CH2:10][C@@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][N:12]1[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)(=[O:29])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 67092838HCID 67092838, compound

Product 1

HCID 86652374HCID 86652374, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-((2R,4R)-4-(benzyloxy)-1-(4-bromophenyl)pyrrolidin-2-yl)acetonitrile: To a solution of 32C (0.38 g, 1.049 mmol) in dichloromethane (5.24 mL) at 0° C. was added TEA (0.292 mL, 2.098 mmol), then methanesulfonyl chloride (0.123 mL, 1.573 mmol). The reaction mixture was stirred for 1 h, and the mixture was diluted with water and dichloromethane. The layers were extracted and the organic layer was dried (MgSO4) and concentrated to give ((2S,4R)-4-(benzyloxy)-1-(4-bromophenyl)pyrrolidin-2-yl)methyl methanesulfonate (white solid, 0.53 g, 1.204 mmol, 115% yield). This white solid was then dissolved in DMSO (5 mL), and NaCN (0.206 g, 4.20 mmol) was added. The mixture was heated to 50° C. for 4 h. The reaction mixture was diluted with EtOAc, and the organic layer was washed with water, brine, dried and concentrated. Purification via silica gel chromatography gave 32D (colorless oil, 235 mg, 0.633 mmol, 60.3% yield). LC-MS Anal. Calc'd for C19H19BrN2O: 370.07. found [M+H] 372.9.

Workup

  1. extractionThe layers were extracted
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9c8b18784a154031a9c7b58987e44c95
Source dataset
uspto-grants-2012_10
Patent number
US08288404B2

Reaction notes

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