Acetic Acid → HCID 86623332, compound

HRID 1922480Notes

Reaction equation

HRID 1922480 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:24](O)(=O)[CH3:25].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.[OH-].[Na+]>[NH:1]1[C:10](=[O:14])[CH2:11][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]1=2.[N:1]1([CH:20]2[CH2:21][CH2:22][N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH2:18][CH2:19]2)[CH2:25][CH2:24][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]1=2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10328IndolineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86623332HCID 86623332, compoundYield 127%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of compound 1 (1 g, 6.793 mmol), N-tert-Butoxycarbonyl-4-piperidone (1.35 g, 6.793 mmol) and acetic acid (0.44 mL, 6.793 mmol) in 25 mL of 1,2-dichloroethane was cooled to 0° C. and treated with NaBH(OAc)3 (2.16 g, 10.19 mmol). The reaction was brought to room temperature and was stirred for 2 days. The solution was diluted with 3N NaOH solution (125 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with brine (50 mL), dried (Na2SO4) and was concentrated. The crude product was subject to flash chromatography on silica gel using 5% ethyl acetate/hexanes. The sample was concentrated and dried resulting in a colourless viscous liquid, compound 2 (2.12 g, 94%). 1H NMR (CDCl3) δ 7.12-7.08 (m, 2H), 6.93 (d, J=7.8 Hz, 1H), 6.83 (t, J=14.7 Hz, 1H), 4.16-4.13 (m, 2H), 3.42 (tt, J=7.2, 22.2 Hz, 1H), 2.98 (brs, 2H), 2.85-2.75 (m, 4H), 1.88 (d, J=12.0 Hz, 2H), 1.73-1.60 (m, 6H), 1.47 (s, 9H); MS-ESI (m/z, %): 331 (MH+, 17), 275 (100).

Workup

  1. customwas brought to room temperature
  2. extractionextracted with ethyl acetate (200 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationwas concentrated
  6. concentrationThe sample was concentrated
  7. customdried

Sources & evidence

ORD record
ord-8bfaee9105fc42d1bbcaee32f4abfbf5
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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