(S,Z)-tert-butyl 1-benzyl-2-oxo-1,2,3,4,7,8-hexahydroazocin-3-ylcarbamate → HCID 68311021, compound

HRID 529510Notes

Reaction equation

HRID 529510 reaction equation
[CH2:1]([N:8]1[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][C@H:10]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH2:1]([N:8]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[C:9]1=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68292616(S,Z)-tert-butyl 1-benzyl-2-oxo-1,2,3,4,7,8-hexahydroazocin-3-ylcarbamate

Product 1

HCID 68311021HCID 68311021, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (S,Z)-tert-butyl 1-benzyl-2-oxo-1,2,3,4,7,8-hexahydroazocin-3-ylcarbamate (86 mg, 0.26 mmol) and 5% Pd/C (15 mg) in EtOAc (1 mL) was stirred under a hydrogen balloon for 1 hr. The reaction mixture was filtered and the filtrate was concentrated and dried under high vacuum to afford (S)-tert-butyl 1-benzyl-2-oxoazocan-3-ylcarbamate (86 mg, 0.26 mmol, 99% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.42-7.14 (m, 5H), 5.71 (d, J=7.5 Hz, 1H), 5.17 (d, J=14.7 Hz, 1H), 4.72 (t, J=9.4 Hz, 1H), 4.02 (d, J=14.7 Hz, 1H), 3.75 (t, J=14.2 Hz, 1H), 3.17 (d, J=15.7 Hz, 1H), 2.18-1.98 (m, 1H), 1.82-1.34 (m, 7H), 1.47 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-8f09904f25f04cf2aa6dfb4d0828b15c
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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