Isopropanol → 1,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate

HRID 657138Notes

Reaction equation

HRID 657138 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(O)(C)C>C(=O)=O>[OH:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18].[OH:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@@H:3]1[CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 68810490Tert-butyl 3-(benzyloxycarbonylaminomethyl)-4-hydroxy-piperidine-1-carboxylate

Product 2

HCID 866353641,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylateHCID 866353651,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

1,1-Dimethylethyl 4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate was resolved via supercritical fluid chromatography (SFC) using a Chiralpak AD-H 30×250 mm column (20% Isopropanol in CO2; 70 ml/min; 30 deg C.; uv 220 nm) to obtain the E1 (first eluting isomer: 98% ee) and E2 (second eluting isomer; 94% ee) enantiomers presumed 1,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (E2) and presumed 1,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (E1) as white solids.

Sources & evidence

ORD record
ord-41af00076c374fb481be0e84c590c566
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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