Dichloromethane → HCID 43652145, compound

HRID 2111921Notes

Reaction equation

HRID 2111921 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[CH2:29]([NH2:34])[CH2:30][CH:31]([CH3:33])[CH3:32].ClCCl>O.C([O-])(O)=O.[Na+]>[C:18]([O:17][C:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH:34][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:24][CH2:23]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7894IsoamylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43652145HCID 43652145, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Sodium triacetoxyborohydride (24.9 g, 117.48 mmol) is added to a stirred solution of 1-Boc-4-piperidone (15.6 g, 78.3 mmol), iso-amyl amine (10.0 ml, 86.15 mmol), and dichloromethane (400 ml). The reaction is stirred overnight at room temperature under nitrogen. The reaction is diluted with water and aqueous saturated NaHCO3, and extracted with dichloromethane (150 ml×3). The dichloromethane is concentrated under vacuum, diluted with ethyl acetate and washed with aqueous saturated NaHCO3, dried over Na2SO4, filtered, and concentrated to yield (19.99 g) of 4-(3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester: mass spectrum (ion spray): m/z=271 (M+1); 1H NMR (CDCl3): δ=4.05 (2H, brs), 2.84-2.73 (2H, brm), 2.67-2.55 (2H, m), 1.84 (2H, brd), 1.67-1.58 (1H, m), 1.51-1.44 (10H, m), 1.41-1.33 (2H, m), 1.30-1.18 (2H, m), 0.90 (6H, d).

Workup

  1. extractionextracted with dichloromethane (150 ml×3)
  2. concentrationThe dichloromethane is concentrated under vacuum
  3. additiondiluted with ethyl acetate
  4. washwashed with aqueous saturated NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c28b50b39aa04fa08b3279d6b2189428
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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