Hydrochloric Acid → HCID 69818612, compound

HRID 1006334Notes

Reaction equation

[CH:1]([CH:14]1[NH:23][CH:22]2[CH:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[N:16](C(OC(C)(C)C)=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:31]>>[ClH:31].[ClH:31].[CH:1]([CH:14]1[CH2:15][NH:16][CH:17]2[CH:22]([CH2:21][CH2:20][CH2:19][CH2:18]2)[NH:23]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 86589636HCID 86589636, compound

Product 1

HCID 69818612HCID 69818612, compound

Procedure

Tert-Butyl (3RS,4aSR,8aRS)-3-benzhydryloctahydroquinoxaline-1-carboxylate (100 mg) was dissolved in hydrogen chloride (5 ml, 4N solution in ethyl acetate) and the mixture was stirred at ambient temperature for 3 hours. The volatile materials were removed under reduced pressure to give (2RS,4aRS,8aSR)-2-benzhydryldecahydroquinoxaline dihydrochloride, which was dissolved in water and washed with ethyl acetate. The aqueous phase was adjusted to pH 9-10 and extracted with ethyl acetate three times. The combined extract was washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give (2RS,4aRS,8aSR)-2-benzhydryldecahydroquinoxaline (88 mg).

Workup

customThe volatile materials were removed under reduced pressure

Sources & evidence

ORD record: ord-b6bb2f67024f41129106dc69f47f8de2
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787543B2

Reaction notes

Loading…