1-Iodopropane → HCID 11674308, compound

HRID 2100604Notes

Reaction equation

HRID 2100604 reaction equation
I[CH2:2][CH2:3][CH3:4].[Cl:5][C:6]1[C:15]2[C:14](=[O:16])[NH:13][C@H:12]3[CH2:17][N:18](C(OC(C)(C)C)=O)[CH2:19][C@@H:11]3[C:10]=2[CH:9]=[C:8]([CH2:27][CH3:28])[CH:7]=1>>[ClH:5].[Cl:5][C:6]1[C:15]2[C:14](=[O:16])[N:13]([CH2:2][CH2:3][CH3:4])[C@H:12]3[CH2:17][NH:18][CH2:19][C@@H:11]3[C:10]=2[CH:9]=[C:8]([CH2:27][CH3:28])[CH:7]=1

Participants

3

Reactant 2

HCID 336431-IodopropaneHCID 69057658HCID 69057658, compound

Product 1

HCID 11674308HCID 11674308, compound

Procedure

Following the procedures described in Example 24, Parts A and B, except that iodopropane was used instead of iodomethane, (3aR,9bS)-tert-butyl 6-chloro-5-oxo-8-ethyl-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the first eluting compound from the OD column separation of N-BOC intermediate enantiomers in Example 29 and 30 (the first eluting compound gave Example 29), was converted to the title compound of Example 42 as an off-white solid. 1H NMR (CD3OD): δ 7.37 (s, 1H), 7.32 (s, 1H), 4.48 (q, 1H, J=6.8 Hz), 3.98-3.92 (m, 1H), 3.80-3.69 (overlapping m, 4H), 3.41-3.35 (m, 1H), 3.35-3.30 (m, 1H), 2.71 (q, 2H, J=7.5 Hz), 1.72-1.60 (m, 2H), 1.27 (t, 3H, J=7.7 Hz), 0.96 (t, 3H, J=7.4 Hz). LRMS (ESI): 293.2/295.2 (M+H)+.

Workup

  1. customthe first eluting compound from the OD column separation of N-BOC intermediate enantiomers in Example 29 and 30 (the first eluting compound
  2. customgave Example 29),

Sources & evidence

ORD record
ord-e1dbc0fbb08f45c1ab593b6ce1d3a455
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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