Triethylamine → HCID 178525120, compound

HRID 2205641Notes

Reaction equation

HRID 2205641 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.O=[CH:11][CH2:12][C:13]1([C:29](OCC)=[O:30])[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:14]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[OH:9][C@@H:6]1[CH2:7][CH2:8][C@H:3]([N:2]2[CH2:11][CH2:12][C:13]3([CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[O:20])[CH2:14]3)[C:29]2=[O:30])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 598689161-Benzyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylateHCID 178479277HCID 178479277, compound

Product 1

HCID 178525120HCID 178525120, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of cis-4-aminocyclohexanol hydrochloride (Available from Sijia Medchem Lab, China) (13.8 g, 0.0910 mol) and 1-benzyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylate (31.0 g, 0.0930 mol) in 1,2-dichloroethane (250 mL) was added triethylamine (23.3 mL, 0.167 mol) at room temperature. The mixture was stirred at 40° C. overnight. Sodium triacetoxyborohydride (Aldrich, cat #: 316393) (49.3 g, 0.232 mol) was added to the above mixture and stirred at r.t. for 1 h. LC/MS data indicated that the starting material was consumed, and an intermediate product with m/e: 433.2 (M+H)+ was observed.

Workup

  1. stirringstirred at r.t. for 1 h
  2. customwas consumed

Sources & evidence

ORD record
ord-100f236ec828480ba49df12bb8cb8442
Source dataset
uspto-grants-2016_06
Patent number
US09371323B2

Reaction notes

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