Hydrogen Bromide → HCID 178511505, compound

HRID 2273243Notes

Reaction equation

HRID 2273243 reaction equation
Br.C(OC(=O)[NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH:15]2[CH2:28][C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([O:29]C)[CH:25]=4)[N:20]=[CH:19][C:18]=3[O:17][CH2:16]2)[CH2:11][CH2:10]1)(C)(C)C>C(O)(=O)C>[NH2:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([CH:15]2[CH2:28][C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([OH:29])[CH:25]=4)[N:20]=[CH:19][C:18]=3[O:17][CH2:16]2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178487793HCID 178487793, compound

Product 1

HCID 178511505HCID 178511505, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

47% Hydrobromic acid (36 mL, 0.33 mol, 75.0 eq) is added at room temperature to a stirred solution of [trans-4-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-yl)-cyclohexyl]-carbamic acid tert-butyl ester (1.8 g, 4.36 mmol, 1.0 eq) in acetic acid (25 mL). After 18 hours stirring at 130° C., the reaction mixture is cooled down to 0° C. and the resulting precipitate is collected by filtration, washed with acetonitrile and dried under high vacuum to afford 3-(trans-4-amino-cyclohexyl)-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-6-ol as a light yellow solid (1.13 g, 87% yield).

Workup

  1. temperaturethe reaction mixture is cooled down to 0° C.
  2. filtrationthe resulting precipitate is collected by filtration
  3. washwashed with acetonitrile
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-ad5deefc146041568f75210aa06066ad
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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