Ethanol → (3R,4R)-Benzyl 4-((tert-butoxycarbonyl)amino)-3-hydroxypiperidine-1-carboxylate

HRID 69892Notes

Reaction equation

HRID 69892 reaction equation
C(OC(N[C@@H:9]1[C@@H:14](O)[CH2:13][CH2:12][N:11]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10]1)=O)(C)(C)C.[C:26]([O:30][C:31]([NH:33][C@H]1[C@H](O)CCN(C(OCC2C=CC=CC=2)=O)C1)=[O:32])([CH3:29])([CH3:28])[CH3:27].CCCCCCC.C([OH:60])C>>[C:26]([O:30][C:31]([NH:33][C@@H:14]1[CH2:13][CH2:12][N:11]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:10][C@H:9]1[OH:60])=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 4

HCID 702EthanolHCID 8900HeptaneHCID 53487823Benzyl (3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylateHCID 58423176Phenylmethyl (3S,4S)-3-(((1,1-dimethylethoxy)carbonyl)amino)-4-hydroxy-1-piperidinecarboxylate

Product 1

HCID 58745562(3R,4R)-Benzyl 4-((tert-butoxycarbonyl)amino)-3-hydroxypiperidine-1-carboxylate

Procedure

The enantiomerically pure (3S,4S)-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylate and (3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylate were resolved by chiral HPLC (For analysis Rt=6.8 min and 9.1 min respectively; n-heptane:ethanol=70:30 (v:v), Chiralpak AD-H prep 250×4.6 mm at 1 mL/min. For preparative separation, n-heptane:ethanol=80:20 (v:v), Chiralpak AS 50×500 mm at 90 mL/min).

Workup

  1. customFor analysis Rt=6.8 min and 9.1 min
  2. customFor preparative separation, n-heptane

Sources & evidence

ORD record
ord-4e7e03cf29ce4100a8879554cb3515f1
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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