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Methyl chloroformate → HCID 59201624, compound

HRID 451690
Notes
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Reaction equation

HRID 451690 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C@@H:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[F:26])[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1.CCN(CC)CC.Cl[C:35]([O:37][CH3:38])=[O:36]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:26][C:20]1[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:19]=1[C@H:5]([O:4][CH2:3][CH2:2][NH:1][C:35]([O:37][CH3:38])=[O:36])[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 59201622HCID 59201622, compound

Product 1

HCID 59201624HCID 59201624, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of (R)-tert-butyl 3-((R)-(2-aminoethoxy)(2,3-difluorophenyl)methyl)piperidine-1-carboxylate (195 mg, 0.402 mmol), DMAP (25.8 mg, 0.201 mmol) and Et3N (0.18 mL) in dry CH2Cl2 at 0° C. was added methyl chloroformate (189 mg, 2.013 mmol), the mixture was allowed to warm to rt and stirred overnight. The mixture was concentrated in vacuo to give the crude product (R)-tert-butyl 3-((R)-(2,3-difluorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate (168 mg, 98%), which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 7.21 (m, 3H), 4.57 (m, 1H), 4.44 (d, 1H), 4.08 (m, 1H), 3.82 (m, 1H), 3.53 (s, 3H), 3.29 (d, 2H), 2.93 (m, 2H), 1.79 (m, 1H), 1.63 (m, 1H), 1.43 (s, 9H), 1.34 (m, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f60789b69265455d8bab9128790b2a09
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08487108B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes