Borane → (S)-benzyl 4-benzyl-2,2-dimethylmorpholine-3-carboxylate

HRID 524616Notes

Reaction equation

HRID 524616 reaction equation
[CH2:1]([N:8]1[C:13](=O)[CH2:12][O:11][C:10]([CH3:16])([CH3:15])[C@H:9]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C:10]([CH3:16])([CH3:15])[C@H:9]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 118118261(S)-benzyl 4-benzyl-2,2-dimethyl-5-oxomorpholine-3-carboxylate

Product 1

HCID 118118262(S)-benzyl 4-benzyl-2,2-dimethylmorpholine-3-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-benzyl 4-benzyl-2,2-dimethyl-5-oxomorpholine-3-carboxylate (163 g, 461 mmol) was reacted with a solution of borane in THF (1 mol/L, 692 mL) according to the procedure as described in Example 34, Step B to give the title compound as colorless oil (133 g, 85%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-f94aebf655b841afa8af0b62e3404760
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

Loading…