Lithium borohydride → HCID 13008958, compound

HRID 1670611Notes

Reaction equation

HRID 1670611 reaction equation
[BH4-].[Li+].C[O:4][C:5]([C@@H:7]1[CH2:11][C@H:10]([N:12]=[N+:13]=[N-:14])[CH2:9][N:8]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O>C(OCC)C>[C:18]([O:17][C:15]([N:8]1[CH2:9][C@@H:10]([N:12]=[N+:13]=[N-:14])[CH2:11][C@H:7]1[CH2:5][OH:4])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Product 1

HCID 13008958HCID 13008958, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add lithium borohydride (0.16 mol, 3.6 g) to a solution of (2S,4S)-4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.16 mol, 40 g) in anhydrous diethyl ether (400 mL) at −10 to −20° C. under a nitrogen atmosphere. Upon complete addition, stir the reaction mixture for 30 min at the same temperature. Quench the reaction mixture with saturated sodium bicarbonate solution at −70° C. and allow it to come to room temperature slowly. Separate the organic layer and extract the aqueous layer with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under vacuum to obtain the title compound (32 g, crude) as a thick, yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 2.32-2.35 (m, 1H), 3.30 (dd, 1H), 3.65-3.79 (m, 4H), 4.07-4.29 (m, 2H).

Workup

  1. additionUpon complete addition
  2. customQuench the reaction mixture with saturated sodium bicarbonate solution at −70° C.
  3. customto come to room temperature
  4. customSeparate the organic layer
  5. extractionextract the aqueous layer with dichloromethane
  6. dry with materialDry the organic layer over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-7ac5531ea9094fd189e209994f826173
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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