Methanol → tert-Butyl (1R,3S,6S)-3-(hydroxymethyl)-2-azabicyclo[4.1.0]heptane-2-carboxylate

HRID 705714Notes

Reaction equation

HRID 705714 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:14]([C:15](O)=[O:16])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15][OH:16])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 89872562(1R,3S,6S)-2-(tert-butoxycarbonyl)-2-azabicyclo[4.1.0]heptane-3-carboxylic acid

Product 1

HCID 89872603tert-Butyl (1R,3S,6S)-3-(hydroxymethyl)-2-azabicyclo[4.1.0]heptane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of D5 (11 g, 45.6 mmol) in THF (350 mL) cooled at 0° C., BH3 1M in THF (90 mL, 90 mmol) was added and the mixture was stirred at room temperature for 2 hours. Methanol (50 mL) was added; this solution was concentrated and co-evaporated twice from methanol to give the title compound. Yield (11 g, 100%).

Workup

  1. concentrationthis solution was concentrated and co-evaporated twice from methanol

Sources & evidence

ORD record
ord-4089039aaccb46c68cc151624d3004ee
Source dataset
uspto-grants-2015_11
Patent number
US09174977B2

Reaction notes

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