6-Tert-butoxycarbonylamino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester → (3S,6S,10aS)-6-amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester

HRID 1824419Notes

Reaction equation

HRID 1824419 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[N:9]2[C:10](=[O:24])[CH:11]([NH:16]C(OC(C)(C)C)=O)[CH2:12][CH:13]=[CH:14][CH2:15][CH:8]2[CH2:7][CH2:6]1)=[O:4]>FC(F)(F)C(O)=O.C(Cl)Cl>[CH3:1][O:2][C:3]([C@H:5]1[N:9]2[C:10](=[O:24])[C@@H:11]([NH2:16])[CH2:12][CH:13]=[CH:14][CH2:15][C@@H:8]2[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 1

HCID 695843536-Tert-butoxycarbonylamino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester

Product 1

HCID 69584382(3S,6S,10aS)-6-amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

6-tert-butoxycarbonylamino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester, 7, (3.46 g, 10.2 mmol) is treated with a solution of 1:1 trifluoroacetic acid/CH2Cl2 (50 mL) and allowed to stir for 2 hours at room temperature after which the solution is concentrated in vacuo and the resulting residue purified over silica (5% methanol/methylene chloride) to afford 2.43 g (100% yield) of the desired product as dark orange crystals. 1H NMR (CDCl3): δ 8.11 (bs, 2H), 5.76 (m, 2H), 4.66 (dd, J=9.3, 6.0 Hz, 1H), 4.50 (dd, J=8.7, 3.6, 1H), 4.21 (m, 1H), 3.68 (s, 3H), 2.95 (m, 1H), 2.73 (dt, J=15.3, 6.0, 1H), 2.43 (m, 2H), 2.15 (m, 2H), 1.94 (m, 2H). 13C NMR (CDCl3): δ 172.3, 168.5, 127.1, 60.7, 58.7, 52.3, 51.9, 32.7, 32.6, 31.2, 27.3. ESI MS 239.12 (M+H).

Workup

  1. concentrationis concentrated in vacuo
  2. customthe resulting residue purified over silica (5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-594d92fbc0f54b04b23a66d740163b1a
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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