Acetic Acid → HCID 57449817, compound

HRID 2353145Notes

Reaction equation

HRID 2353145 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:12][CH2:13]1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57449817HCID 57449817, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-BOC-4-formyl-piperidine (210 mg) in dry 1,2-dichloroethane (10 mL), was added morpholine (86 mg) and glacial acetic acid (60 μL) and stirred for 1 h at room temperature. To the mixture was added sodium triacetoxyborohydride (272 mg) and the mixture stirred for 12 h. The reaction mixture was extracted into DCM (25 mL), washed with 50% sodium bicarbonate solution (10 mL), brine (10 mL), and dried (MgSO4). The solvents were removed in vacuo to give a residue which was purified by flash chromatography to give 4-morpholine-4-ylmethyl-piperidine-1-carboxylic acid tert-butyl ester (120 mg). Treatment with TFA yielded the desired amine which was isolated as the TFA salt.

Workup

  1. stirringthe mixture stirred for 12 h
  2. extractionThe reaction mixture was extracted into DCM (25 mL)
  3. washwashed with 50% sodium bicarbonate solution (10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvents were removed in vacuo
  6. customto give a residue which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3f5018f8cf6a4d04900d4def4268a0b3
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

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