Trityl chloride → (2R,4R)-4-Hydroxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester

HRID 2217473Notes

Reaction equation

HRID 2217473 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1)=[O:4].C(N(CC)CC)C.[C:18]1([C:24](Cl)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:4]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 7020012(2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate

Product 1

HCID 68685802(2R,4R)-4-Hydroxy-1-trityl-pyrrolidine-2-carboxylic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into a solution of 1 (10 g, 55 mmol) in anhydrous CHCl3 (100 mL) was added triethylamine (19 mL, 138 mmol) and triphenylmethyl chloride (14.5 g, 52 mmol). The mixture was stirred at RT for 3d before concentrating and redissolving in EtOAc. The solution was washed sequentially with 10% aq. citric acid, water, and brine before drying over MgSO4 and concentrating under reduced pressure to give 2 (20 g, 100%) as a yellow solid.

Workup

  1. concentrationbefore concentrating
  2. dissolutionredissolving in EtOAc
  3. washThe solution was washed sequentially with 10% aq. citric acid, water, and brine
  4. dry with materialbefore drying over MgSO4
  5. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-ddb961864d9044f79987a231a9bb47bb
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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