Water → 1,1-Dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)[1-(2-hydroxy-1-{[(phenylmethyl)oxy]methyl}ethyl)-4-piperidinyl]carbamate
Reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:13]3[CH2:18][CH2:17][N:16]([CH:19]([CH2:24][O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:20](OC)=[O:21])[CH2:15][CH2:14]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([CH:13]3[CH2:18][CH2:17][N:16]([CH:19]([CH2:24][O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:20][OH:21])[CH2:15][CH2:14]3)[C:33](=[O:34])[O:35][C:36]([CH3:38])([CH3:39])[CH3:37])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A solution of methyl 2-[4-((2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl){[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-3-[(phenylmethyl)oxy]propanoate (618 mg, 1.141 mmol) in dry THF (8 ml) at −78° C. under Ar was added LiAlH4 (1.312 ml, 1.312 mmol) dropwise. The reaction mixture was allowed to warm to ˜−10° C. over 2 h. The mixture was then stirred at 0° C. for 2 h before addition of water (0.1 ml), then sodium hydroxide (0.18 ml, 0.360 mmol) and then water (0.2 ml). The mixture was then stirred for a further 2 h at rt. The resulting mixture was filtered and washed with THF (100 ml). The combined filtrate and washings were evaporated under reduced pressure to afford the product (0.519 g, 89% yield).
Workup
- filtrationThe resulting mixture was filtered
- washwashed with THF (100 ml)
- customThe combined filtrate and washings were evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-34b38ae9cac046efa6e6dd786724feab
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389524B2
Reaction notes
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