Water → Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1087628Notes

Reaction equation

HRID 1087628 reaction equation
B.[C:2]([N:12]1[CH2:19][CH:18]([OH:20])[CH2:17][C@H:13]1[C:14](O)=[O:15])([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].O>C1COCC1>[OH:15][CH2:14][C@@H:13]1[CH2:17][C@@H:18]([OH:20])[CH2:19][N:12]1[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 12731799(2S)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 14994791Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 200 ml (0.2 mol) of borane. THF complex was added 27.8 g (0.1 mol) of 1-(carbobenzyloxy)-4-hydroxy-L-proline in 50 ml of THF at 0° C. After 16 hours of stirring at room temperature, 100 ml of water was added carefully followed by 12 ml of 6N aqueous HC1 solution and the mixture was extracted with 3 x 100 ml of methylene chloride. The combined organic extracts were dried over MgSO4 and evaporated to yield 22.6 g of the product (oil, 90% yield). NMR(CDC13) 7.40 (m,5H), 5.10 (m,2H), 4.90 (m,1H), 4.65 (m,1H), 4.35 (m,1H), 4.17 (m,1H), 3.60 (m,3H), 2.05 (m,1H), 1.70 (m,1H).

Workup

  1. extractionthe mixture was extracted with 3 x 100 ml of methylene chloride
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-b0d599bc875c4217ae49d4e31f1fe12f
Source dataset
uspto-grants-1991_07
Patent number
US05036153

Reaction notes

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