Lithium borohydride → HCID 57659761, compound

HRID 1011610Notes

Reaction equation

HRID 1011610 reaction equation
[Li+].[BH4-].[CH:3]1([C@H:6]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:9]([C:18](OC)=[O:19])[C:8](=[O:22])[CH2:7]2)[CH2:5][CH2:4]1>C1COCC1.CCOC(C)=O>[CH:3]1([C@H:6]2[N:10]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH:9]([CH2:18][OH:19])[CH:8]([OH:22])[CH2:7]2)[CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 57659775HCID 57659775, compound

Product 1

HCID 57659761HCID 57659761, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

LiBH4 (0.5 g, 23.3 mmol) was added to a solution of (5S)-1-tert-butyl 2-methyl 5-cyclopropyl-3-oxopyrrolidine-1,2-dicarboxylate (31) (2.2 g, 7.76 mmol) in THF (20 mL). The reaction mixture was stirred at 60° C. for 18 h after which HPLC indicated that the reaction was compete. The resulting solution was diluted with EtOAc (20 mL) and washed with sat. aq. NaHCO3 (20 mL). The organic phase was dried (Na2SO4), filtered and concentrated under vacuum to give (5S)-tert-butyl 5-cyclopropyl-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (32). Retention time (min)=1.484 method [1], MS (m/z) 280.2 (M+Na)+.

Workup

  1. washwashed with sat. aq. NaHCO3 (20 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e71650af12a0413381aa6e1855fea516
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

Loading…