HCID 21709010, compound → 5-(Tert-butyloxycarbonyl)-7-hydroxy-1-[((methanesulfonyl)oxy)methyl]-1,2,3,4-tetrahydro-5h-naphtho[1,2-b]azepine

HRID 651869Notes

Reaction equation

HRID 651869 reaction equation
C([O:8][C:9]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:12]2[N:13]([CH2:25][O:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:14][CH2:15][CH2:16][CH:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]=2[CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[C:21]([O:20][C:18]([CH:17]1[CH2:16][CH2:15][CH2:14][N:13]([CH2:25][O:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:12]2[C:31]3[C:36]([C:9]([OH:8])=[CH:10][C:11]1=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 1

HCID 21709010HCID 21709010, compound

Product 1

HCID 217090075-(Tert-butyloxycarbonyl)-7-hydroxy-1-[((methanesulfonyl)oxy)methyl]-1,2,3,4-tetrahydro-5h-naphtho[1,2-b]azepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 84 (0.096 g, 0.188 mmol, 1 equiv) in THF (3.0 mL) was treated with 10% Pd—C (0.042 g, 0.04 mmol, 0.2 equiv) followed by aqueous HCO2NH4 (1.0 mL, 25% w/v, 21 equiv) and the resulting mixture was stirred at 25° C. for 2.5 h. The mixture was filtered through Celite to afford a biphasic filtrate which was partitioned. The aqueous phase was extracted with EtOAc (2×2 mL) and the combined organic portions were dried (MgSO4), filtered, and concentrated to give 85 as an analytically pure white solid (0.072 g, 0.079 g theoretical, 91%): mp 141-142° C.; 1H NMR 400 MHz, DMF-d7) major rotamer δ 8.29 (d, J=8.2 Hz, 1H), 8.26 (d, J=8.7 Hz, 1H), 7.62-7.59 (m, 1H), 7.54-7.50 (m, 1H), 6.82 (s, 1H), 4.59-4.47 (m, 1H), 4.43-4.25 (m, 3H), 3.02 (s, 3H), 2.98-2.76 (m, 1H), 2.35-2.20 (m, 1H), 2.13-1.95 (m, 1H), 1.71-1.67 (m, 2H), 1.39 (s, 9H); 13C NMR (100 MHz, DMF-d7)major rotamer δ 154.0, 153.5, 141.8, 134.0, 127.7, 125.2, 125.1, 124.3, 123.3, 123.0, 110.3, 80.4, 71.4, 48.2, 36.8, 36.4, 28.2 (3C), 27.2, 25.0; IR (film) νmax 3262, 2974, 2933, 2872, 1692, 1662, 1594 cm−1; FABHRMS (NBA-NaI) m/z 444.1468 (M+Na+, C21H27NO6S requires 444.1457).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto afford a biphasic filtrate which
  3. customwas partitioned
  4. extractionThe aqueous phase was extracted with EtOAc (2×2 mL)
  5. dry with materialthe combined organic portions were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-276be84a843a4105a4430e522cf3e462
Source dataset
uspto-grants-2001_08
Patent number
US06281354B1

Reaction notes

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