Iodoethane → HCID 11573245, compound

HRID 2100603Notes

Reaction equation

HRID 2100603 reaction equation
I[CH2:2][CH3:3].[Cl:4][C:5]1[C:14]2[C:13](=[O:15])[NH:12][C@H:11]3[CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][C@@H:10]3[C:9]=2[CH:8]=[C:7]([CH2:26][CH3:27])[CH:6]=1>>[ClH:4].[Cl:4][C:5]1[C:14]2[C:13](=[O:15])[N:12]([CH2:2][CH3:3])[C@H:11]3[CH2:16][NH:17][CH2:18][C@@H:10]3[C:9]=2[CH:8]=[C:7]([CH2:26][CH3:27])[CH:6]=1

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 69057658HCID 69057658, compound

Product 1

HCID 11573245HCID 11573245, compound

Procedure

Following the procedures described in Example 24, Parts A and B, except that iodoethane 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 41 as an off-white solid. 1H NMR (CD3OD): δ 7.28 (s, 1H), 7.22 (s, 1H), 4.43-4.37 (m, 1H), 3.88-3.81 (m, 1H), 3.73-3.68 (m, 1H), 3.69 (q, 2H), 3.63 (dd, 1H, J=7.8, 12.3 Hz), 3.45-3.38 (m, 1H), 3.26-3.20 (m, 1H), 2.61 (q, 2H, J=7.5 Hz), 1.17 (t, 3H, J=7.7 Hz), 1.14 (t, 3H, J=7.5 Hz). LRMS (ESI): 279.2/281.2 (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-e731298399a64940aca79c122c6d0e72
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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