Benzyl Bromide → HCID 11559864, compound

HRID 2100605Notes

Reaction equation

HRID 2100605 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[C:19]2[C:18](=[O:20])[NH:17][C@H:16]3[CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][C@@H:15]3[C:14]=2[CH:13]=[C:12]([CH2:31][CH3:32])[CH:11]=1>>[ClH:9].[CH2:1]([N:17]1[C@H:16]2[CH2:21][NH:22][CH2:23][C@@H:15]2[C:14]2[CH:13]=[C:12]([CH2:31][CH3:32])[CH:11]=[C:10]([Cl:9])[C:19]=2[C:18]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 69057658HCID 69057658, compound

Product 1

HCID 11559864HCID 11559864, compound

Procedure

Following the procedures described in Example 24, Parts A and B, except that benzyl bromide 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 43 as an off-white solid. 1H NMR (CD3OD): δ 7.40 (s, 1H), 7.38-7.24 (m, 5H), 7.01 (s, 1H), 5.09 and 4.67 (ABq, 2H, JAB=15.7 Hz), 4.04 (dd, 1H, J=7.4, 11.3 Hz), 3.88-3.81 (m, 1H), 3.65-3.55 (m, 2H), 3.40-3.32 (m, 2H), 2.70 (q, 2H, J=7.5 Hz), 1.25 (t, 3H, J=7.7 Hz). LRMS (ESI): 341.3/343.3 (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-8a72d20126694a43874e2a5927868552
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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