Methanol → N-(tert-Butoxycarbonyl)-D-prolinol

HRID 653840Notes

Reaction equation

HRID 653840 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@@H:12]([C:13](O)=[O:14])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].CO>O1CCCC1>[OH:14][CH2:13][C@H:12]1[CH2:11][CH2:10][CH2:9][N:8]1[C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7]

Participants

4

Reactant 2

HCID 887MethanolHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 688279N-(tert-Butoxycarbonyl)-D-prolinolYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 25.0 g of N-α-t-BOC-D-proline in 250 ml of tetrahydrofuran which is cooled to 0° C. is added dropwise 15 ml of 10M borane-methyl sulfide complex. The reaction is kept at around -20° C. during the addition followed by warming to room temperature and then is gently refluxed for one hour. The mixture is cooled to 0° C., 250 ml of methanol is added carefully and the reaction is evaporated in vacuo to give 23.3 g of a colorless oil which crystallizes on standing to a colorless solid, mp 50°-53° C., [α]D26° =+47°±1 (C=1.162%, methylene chloride).

Workup

  1. additionis added dropwise 15 ml of 10M borane-methyl sulfide complex
  2. additionThe reaction is kept at around -20° C. during the addition
  3. temperatureis gently refluxed for one hour
  4. temperatureThe mixture is cooled to 0° C.
  5. customthe reaction is evaporated in vacuo

Sources & evidence

ORD record
ord-5c37d04b3ac64865aac5de89e7f34887
Source dataset
uspto-grants-1992_07
Patent number
US05128483

Reaction notes

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