Triethylamine → 1,1-Dimethylethyl 4-[(1-cyclobutyl-4-piperidinyl)methyl]-1-piperidinecarboxylate

HRID 1869623Notes

Reaction equation

HRID 1869623 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1.[C:21]1(=O)[CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:21]1([N:1]2[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]3[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]3)[CH2:5][CH2:6]2)[CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 497611974-Piperidin-4-ylmethyl-piperidine-1-carboxylic acid t-butyl ester

Product 1

HCID 688866201,1-Dimethylethyl 4-[(1-cyclobutyl-4-piperidinyl)methyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-(4-piperidinylmethyl)-1-piperidinecarboxylate (may be prepared as described in Description 2) (4.8 g), cyclobutanone (3.81 ml) and triethylamine (4.7 ml) were stirred in DCM (200 ml) at room temperature. After 10 min sodium triacetoxyborohydride (7.2 g) was added and the reaction was stirred at room temperature overnight. The reaction mixture was evaporated and redissolved in dichloromethane (50 ml). After washing with saturated potassium carbonate solution (2×50 ml), saturated sodium hydrogen carbonate solution (2×50 ml) and saturated brine (50 ml) the organic phase was dried (MgSO4) and evaporated to give the title compound (D5) as a colourless solid (5.72 g).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionredissolved in dichloromethane (50 ml)
  3. washAfter washing with saturated potassium carbonate solution (2×50 ml), saturated sodium hydrogen carbonate solution (2×50 ml) and saturated brine (50 ml) the organic phase
  4. dry with materialwas dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-077f1b4d6a6c4af9b54980b4a66a9fc8
Source dataset
uspto-grants-2009_12
Patent number
US07638631B2

Reaction notes

Loading…