Triethylamine → HCID 57659372, compound

HRID 1009817Notes

Reaction equation

HRID 1009817 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C@@H:12]3[C@@H:8]([CH2:9][C:10](=[O:19])[NH:11]3)[CH2:7]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:27](=O)([O:33]C(C)(C)C)[O:28][C:29]([CH3:32])([CH3:31])[CH3:30]>ClCCl>[O:19]=[C:10]1[CH2:9][C@@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:4]3([CH2:7]2)[CH2:3][CH2:2][N:1]([C:27]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:33])[CH2:6][CH2:5]3)[NH:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 57659370HCID 57659370, compound

Product 1

HCID 57659372HCID 57659372, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the (3aR,9bS)-1,3a,4,9b-tetrahydrospiro[benzo[g]indole-5,4′-piperidin]-2(3H)-one (900 mg, 3.51 mmol) in dichloromethane (100 ml) was treated with triethylamine (3 ml) and di-tert-butyl carbonate (1.5 g, 6.8 mmol) at room temperature for 1 h. The reaction mixture was diluted with dichloromethane, washed with aqueous saturated NH4Cl. The organic phase was separated and the aqueous phase was re-extracted with dichloromethane (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated. The residue was purified by flasj chromatography (40 g silica gel, CH2Cl2/CH3CN up to 0:100%) to give (3aR,9bS)-tert-butyl 2-oxo-1,2,3,3a,4,9b-hexahydrospiro[benzo[g]indole-5,4′-piperidine]-1′-carboxylate 12 (700 mg). LC-MS: m/e=301.5 (M−t-Bu+H, 100%). Rt=3.04 min. 1H NMR (300 MHz, CDCl3): 7.36 (d, 1H), 7.25 (td, 1H), 7.21-7.13 (m, 2H), 6.32 (s, 1H, NH), 4.71 (d, J=5.8 Hz, 1H, CHN), 4.02 (br. d, 1H), 3.90 (br. d, 1H), 3.01 (td, J=13.4, 2.8 Hz, 1H), 2.89 (td, J=13, 3.1 Hz, 1H), 2.73-2.62 (m, 1H), 2.29 (td, J=12.7, 5.0 Hz, 1H), 2.23-2.44 (m, 3H), 1.66-1.59 (m, 1H), 1.51 (dd, J=13.2, 4.3 Hz, 1H), 1.41 (s, 9H), 1.37-1.30 (m, 2H).

Workup

  1. washwashed with aqueous saturated NH4Cl
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was re-extracted with dichloromethane (2×)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flasj chromatography (40 g silica gel, CH2Cl2/CH3CN up to 0

Sources & evidence

ORD record
ord-000ffc998e98491085374b4a9aad4f15
Source dataset
uspto-grants-2011_07
Patent number
US07973162B2

Reaction notes

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