Hydrochloric Acid → HCID 11681309, compound

HRID 2100611Notes

Reaction equation

HRID 2100611 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[C:10]2[C:9](=[O:17])[NH:8][C@@H:7]3[CH2:18][N:19](C(OC(C)(C)C)=O)[CH2:20][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2].[ClH:28]>C(OCC)C>[ClH:28].[CH2:1]([C:3]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[C:10]2[C:9](=[O:17])[NH:8][C@@H:7]3[CH2:18][NH:19][CH2:20][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69054341HCID 69054341, compound

Product 1

HCID 11681309HCID 11681309, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3aS,9bR)-tert-butyl 8-ethyl-5-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the second eluting peak from Example 45, Part H (63 mg, 0.16 mmol) in 2 mL of diethyl ether was added 1 mL of 12 N HCl. The resulting mixture was stirred vigorously for 5 min at ambient temperature and then was concentrated and dried in vacuo. The resulting white solid was triturated twice with diethyl ether and dried in vacuo to afford 45 mg (86%) of the title compound of Example 46 as a white solid. 1H NMR (DMSO-D6): δ 9.83 (broad s, 1H), 9.64 (broad s, 1H), 8.89 (s, 1H), 7.66 (s, 1H), 7.43 (s, 1H), 3.95-3.90 (m, 1H), 3.63-3.58 (m, 1H), 3.51-3.45 (m, 1H), 3.34-3.28 (m, 1H), 3.21-3.10 (m, 2H), 2.73 (q, 2H, J=7.7 Hz), 1.21 (t, 3H, J=7.7 Hz). LRMS (ESI): 285.2 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. customdried in vacuo
  3. customThe resulting white solid was triturated twice with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4196111d984d429e8bce71d7feb28f02
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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