2-Bromoethanol → Methyl(3R,4R)-4-{[(benzyloxy)carbonyl]amino}-1-(2-hydroxyethyl)piperidine-3-carboxylate

HRID 255197Notes

Reaction equation

HRID 255197 reaction equation
C(OC(N[C@@H]1CCNC[C@@H]1C(OC)=O)=O)C1C=CC=CC=1.C(N(CC)C(C)C)(C)C.BrCCO.[CH2:35]([O:42][C:43]([NH:45][C@@H:46]1[CH2:51][CH2:50][N:49]([CH2:52][CH2:53][OH:54])[CH2:48][C@@H:47]1[C:55]([O:57][CH3:58])=[O:56])=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([O:42][C:43]([NH:45][C@@H:46]1[CH2:51][CH2:50][N:49]([CH2:52][CH2:53][OH:54])[CH2:48][C@H:47]1[C:55]([O:57][CH3:58])=[O:56])=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 4

HCID 108982-BromoethanolHCID 81531DiisopropylethylamineHCID 58999552methyl (3S,4R)-4-{[(benzyloxy)carbonyl]amino}piperidine-3-carboxylateHCID 66774341Methyl(3S,4R)-4-{[(benzyloxy)carbonyl]amino}-1-(2-hydroxyethyl)piperidine-3-carboxylate

Product 1

HCID 66775250Methyl(3R,4R)-4-{[(benzyloxy)carbonyl]amino}-1-(2-hydroxyethyl)piperidine-3-carboxylateYield 60%

Procedure

Methyl (3S,4R)-4-{[(benzyloxy)carbonyl]amino}piperidine-3-carboxylate (WO 2005/066176) (2.0 g, 6.84 mmol), N,N-diisopropylethylamine (1.8 mL, 10.26 mmol) and 2-bromoethanol (0.63 mL, 8.9 mmol) were reacted as described for Intermediate 37 to give 1.38 g (60%) of the product as a colorless oil.

Sources & evidence

ORD record
ord-488fc3a4f2e94426916df773fce894c0
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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