Diisopropylethylamine → HCID 178469230, compound

HRID 1044338Notes

Reaction equation

HRID 1044338 reaction equation
CCN(C(C)C)C(C)C.Cl.[NH2:11][C@@H:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]1.O=[CH:20][CH2:21][C:22]1([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.O.CC(O)=O>[OH:18][C@@H:15]1[CH2:16][CH2:17][C@H:12]([NH:11][CH2:20][CH2:21][C:22]2([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[CH2:23]2)[CH2:13][CH2:14]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 579708781-Tert-butyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylateHCID 178479277HCID 178479277, compound

Product 1

HCID 178469230HCID 178469230, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

DIPEA (1.05 eq.) was added to a solution of cis-4-aminocyclohexanol hydrochloride (0.080 g, 0.53 mmol) in methanol (2.0 mL) and stirred for 5 min. To this solution 1-tert-butyl 3-ethyl 3-(2-oxoethyl)-piperidine-1,3-dicarboxylate (0.15 g, 0.5 mmol) was added followed by sodium triacetoxyborohydride (0.21 g, 1.0 mmol) and the mixture was stirred for 2 h. The reaction was acidified by adding AcOH and diluted with water and extracted with ether. The aqueous phase was then basified by adding 1 N NaOH and extracted with ethyl acetate which was then washed with water then brine, dried, and concentrated to give the desired product (0.17 g, 85%). LC-MS: 399.2 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. extractionextracted with ether
  3. additionby adding 1 N NaOH
  4. extractionextracted with ethyl acetate which
  5. washwas then washed with water
  6. dry with materialbrine, dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-28422fb989034c1cb35f62866d72e5e0
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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