Hydrochloric Acid → HCID 69415490, compound

HRID 853092Notes

Reaction equation

HRID 853092 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:23][C@@H:22]([CH3:24])[N:11]2[C:12]3[CH:13]=[C:14]([C:19]([OH:21])=O)[CH:15]=[CH:16][C:17]=3[CH2:18][C@@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25]([NH2:29])[CH2:26][CH2:27][CH3:28].C(N1CCOCC1)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:23][C@@H:22]([CH3:24])[N:11]2[C:12]3[CH:13]=[C:14]([C:19](=[O:21])[NH:29][CH2:25][CH2:26][CH2:27][CH3:28])[CH:15]=[CH:16][C:17]=3[CH2:18][C@@H:10]2[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 8007ButylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69417354HCID 69417354, compound

Product 1

HCID 69415490HCID 69415490, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4R,10aR)-4-Methyl-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indole-2,7-dicarboxylic acid 2-tert-butyl ester (300 mg, 0.9 mmol) was dissolved in dichloromethane (5 mL). N-Butylamine (0.45 mL, 4.5 mmol), 4-ethylmorpholine (0.57 mL, 4.5 mmol) and BOP (0.42 g, 0.95 mmol) was added and the mixture was stirred for 16 h at room temperature. The mixture was added to 1 N hydrochloric acid (20 mL) and extracted with diethylether (2×50 mL). Organic phases were pooled, washed with water, 2 N sodium bicarbonate, water and brine to be finally dried with MgSO4. The solvents were removed in vacuo to yield the title compound as colorless foam (346 mg, 98%); ISP-MS: m/e=332.3 (M+H+).

Workup

  1. extractionextracted with diethylether (2×50 mL)
  2. washwashed with water, 2 N sodium bicarbonate, water and brine
  3. dry with materialto be finally dried with MgSO4
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-930065c2c93244a7a4d502511ef50038
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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