Aniline → HCID 66577566, compound

HRID 73609Notes

Reaction equation

HRID 73609 reaction equation
[OH:1][C@@:2]12[C:11](=O)[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:6][CH2:5][CH2:4][CH2:3]2.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O>[C:14]1([NH:13][C@H:11]2[C@:2]3([OH:1])[C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3]3)[CH2:8][CH2:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 12921402(4aR,8aR)-8a-hydroxyoctahydronaphthalen-1(2H)-one

Product 1

HCID 66577566HCID 66577566, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (4aR,8aR)-8a-hydroxyoctahydronaphthalen-1(2H)-one (0.339 g, 2.015 mmol) and aniline (0.552 mL, 6.05 mmol) in 2% CH3COOH in ACE (20 mL) was stirred for 1 hr at rt. Sodium triacetoxyborohydride (1.37 g, 6.45 mmol) was then added and the mixture was stirred for several hours. The mixture was then quenched with sat'd. aq. NaHCO3 and extracted 3× with CH2Cl2. The combined organics were dried, filtered, and concentrated. The residue was purified by column chromatography on silica gel to give the title compound. 1H NMR (500 MHz, CDCl3) δ 7.12-7.18 (m, 2H), 6.60-6.69 (m, 3H), 1.96-2.04 (m, 1H), 1.73-1.81 (m, 1H), 1.64-1.70 (m, 2H), 1.18-1.60 (m, 12H). HRMS (ES) m/z M+H calc'd: 246.1852. found: 246.1850.

Workup

  1. stirringthe mixture was stirred for several hours
  2. customThe mixture was then quenched with sat'd
  3. extractionaq. NaHCO3 and extracted 3× with CH2Cl2
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b5016f6c52124ff0ab59c5453ffcf0eb
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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