Acetic Anhydride → 4-(Acetyl-cyclopropyl-amino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1947509Notes

Reaction equation

HRID 1947509 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]2[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:27](=[O:29])[CH3:28])[CH:15]2[CH2:16][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 2769591tert-Butyl 4-(cyclopropylamino)piperidine-1-carboxylate

Product 1

HCID 687725164-(Acetyl-cyclopropyl-amino)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyclopropylamino-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 4.2 mmol) in DCM (22 mL) was added DIEA (0.8 mL, 4.6 mmol) and acetic anhydride (0.42 mL, 4.4 mmol). The mixture was stirred (rt, 16 h). After washing the solution with 1 N NaOH and brine, the organic layer was dried and concentrated to an orange oil (1.15 g, 98%). MS (ESI): mass calcd. for C15H26N2O3, 282.19; m/z found, 283.2 [M+H]+.

Workup

  1. washAfter washing the solution with 1 N NaOH and brine
  2. customthe organic layer was dried
  3. concentrationconcentrated to an orange oil (1.15 g, 98%)

Sources & evidence

ORD record
ord-9b7014b6dd8341e88cd311bec1b2a3b3
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

Loading…