Methanol → HCID 89822875, compound

HRID 705720Notes

Reaction equation

HRID 705720 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:14]([C:15](O)=[O:16])[CH2:13][CH2:12][CH:11]2[CH:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C1COCC1>[OH:16][CH2:15][C@@H:14]1[CH2:13][CH2:12][CH:11]2[CH:9]([CH2:10]2)[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

4

Reactant 2

HCID 887MethanolHCID 89822872HCID 89822872, compound

Product 1

HCID 89822875HCID 89822875, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of D6 (8 g, 45.6 mmol) in THF (250 mL) cooled at 0° C., BH3 1M in THF (66 mL, 66 mmol) was added and the mixture was stirred at room temperature for 2 hours. Methanol was added, the solution was concentrated in vacuum and co-evaporated twice from methanol to give the title compound as 1/1 diasteroisomeric mixture. Yield (7.6 g, 100%)

Workup

  1. concentrationthe solution was concentrated in vacuum

Sources & evidence

ORD record
ord-272c494927e245ad936c1d25e48886ce
Source dataset
uspto-grants-2015_11
Patent number
US09174977B2

Reaction notes

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