Triethylamine → HCID 69054993, compound

HRID 2100585Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:20][C@H:19]2[C@@H:10]([N:11]([CH2:26][C:27](O)=[O:28])[C:12](=[O:25])[C:13]3[C:14]([C:21]([F:24])([F:23])[F:22])=[CH:15][CH:16]=[CH:17][C:18]=32)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.O>[OH:28][CH2:27][CH2:26][N:11]1[C@H:10]2[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:20][C@@H:19]2[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:21]([F:23])([F:22])[F:24])[C:13]=2[C:12]1=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-((3aR,9bS)-2-(tert-butoxycarbonyl)-5-oxo-6-(trifluoromethyl)-1,2,3,3a-tetrahydro-5H-pyrrolo[3,4-c]isoquinolin-4(9bH)-yl)acetic acid from Example 19, Part A (70 mg, 0.17 mmol) in 4 mL of THF at 0° C. was added triethylamine (0.028 mL, 0.20 mmol) and ethyl chloroformate (0.019 mL, 0.20 mmol). The reaction was allowed to stir for 30 min at 0° C. and then there was added sodium borohydride (19 mg, 0.51 mmol) in a minimal amount of water. The resulting mixture was stirred for 1 h at 0° C. and then was quenched with 10 mL of 1N HCl. The mixture was extracted with ethyl acetate and the organics were washed with sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 60 mg (88%) of the title compound which was sufficiently pure to be used without purification. LRMS (ESI): 401.21 (M+H)+.

Workup

stirringThe resulting mixture was stirred for 1 h at 0° C.
customwas quenched with 10 mL of 1N HCl
extractionThe mixture was extracted with ethyl acetate
washthe organics were washed with sat'd aq NaHCO3 and brine
dry with materialdried (MgSO4)
filtrationfiltered through a pad of silica gel
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8cf55a0b94e649ba902cdff68fa53d3a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572805B2

Reaction notes

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