Borane → [(4R)-4-Hydroxy-4-(1-methyl-1H-imidazol-2-yl)butyl]carbamic acid 1,1-dimethylethyl ester

HRID 352131Notes

Reaction equation

HRID 352131 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][C:11]([C:13]1[N:14]([CH3:18])[CH:15]=[CH:16][N:17]=1)=[O:12])([CH3:4])[CH3:3].CB1N2CCC[C@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.B>O1CCCC1>[CH3:4][C:2]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][C@@H:11]([OH:12])[C:13]1[N:14]([CH3:18])[CH:15]=[CH:16][N:17]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 6331BoraneHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 131724443[4-(1-Methyl-1H-imidazol-2-yl)-4-oxobutyl]carbamic acid 1,1-dimethylethyl ester

Product 1

HCID 131724444[(4R)-4-Hydroxy-4-(1-methyl-1H-imidazol-2-yl)butyl]carbamic acid 1,1-dimethylethyl esterYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of step (a) (0.60 g, 2.24 mmol) was reacted with (3aS)-tetrahydro-1-methyl-3,3-diphenyl-3H-pyrrolo[1,2-c][1,3,2]oxazaborole (1M in toluene, 0.22 ml) and borane:tetrahydrofuran complex (1M, 1.5 ml, 1.5 mmol) in tetrahydrofuran (40 ml) using the procedure described in Example 1 step (a) to give the sub-title compound as a colourless oil (0.25 g, 42%).

Sources & evidence

ORD record
ord-90377bdae2944e0fb0fbaebc1a0331ad
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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