Potassium Carbonate → Tert-butyl 4-(but-3-ynylamino)piperidine-1-carboxylate

HRID 1424522Notes

Reaction equation

HRID 1424522 reaction equation
Cl.[CH2:2]([NH2:6])[CH2:3][C:4]#[CH:5].C([O-])([O-])=O.[K+].[K+].O=[C:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[CH2:2]([NH:6][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[CH2:3][C:4]#[CH:5]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 12221022But-3-yn-1-amine hydrochloride

Product 1

HCID 64084268Tert-butyl 4-(but-3-ynylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of but-3-yn-1-amine hydrochloride (26.4 g, 0.25 mol), K2CO3 (17.4 g, 0.13 mol), and tert-butyl 4-oxopiperidine-1-carboxylate (41.8 g, 0.21 mol) in MeOH (500 mL) was stirred at rt for 5 hrs. Then, NaBH(OAc)3 (133.6 g, 0.63 mol) was added and the suspension was stirred at rt for 17 hrs. The crude reaction mixture was used directly in the next step. ESI-MS (EI+, m/z): 253.2 [M+H]+.

Workup

  1. stirringthe suspension was stirred at rt for 17 hrs
  2. customThe crude reaction mixture

Sources & evidence

ORD record
ord-15de8f6b1f0b40c4a25c4b89ce7994b4
Source dataset
uspto-grants-2015_01
Patent number
US08927724B2

Reaction notes

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