Water → HCID 67350251, compound

HRID 1675912Notes

Reaction equation

HRID 1675912 reaction equation
C([O:3][C:4]([C:6]1[NH:33][N:32]=[C:31]2[C:7]=1[CH2:8][CH:9]1[CH:22]3[CH:13]([C:14]4[CH:15]=[CH:16][C:17]([O:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[CH:18][C:19]=4[CH2:20][CH2:21]3)[CH2:12][CH2:11][C:10]12[CH3:34])=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[CH2:24]([O:23][C:17]1[CH:16]=[CH:15][C:14]2[CH:13]3[CH:22]([CH2:21][CH2:20][C:19]=2[CH:18]=1)[CH:9]1[CH2:8][C:7]2[C:31]([C:10]1([CH3:34])[CH2:11][CH2:12]3)=[N:32][NH:33][C:6]=2[CH2:4][OH:3])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178470407HCID 178470407, compound

Product 1

HCID 67350251HCID 67350251, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Benzyloxy-6a-methyl-4b,5,6,6a,8,10,10a,10b,11,12-decahydro-7,8diaza-pentaleno[2,1-a]phenanthrene-9-carboxylic acid ethyl ester (457 mg, 1.0 mmol, CAB03049) was added to a suspension of LiAlH4 (100 mg) in THF (20 mL). The mixture was stirred for 30 minutes at room temperature, then water (1 mL) was added (to destroy the excess of LiAlH4). Stirring was continued for 1 hour (light yellowgreen suspension), acetic acid (0.5 mL) was added, the inorganic solids were filtered of and washed carefully with THF (ca. 50 mL).The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was crystallised from ethyl acetate/diethyl ether. Yield: 215 mg (52%) colorless crystals. 1H-NMR (CDCl3, 400 MHz), δ: 1.01 (s, 3H, —CH3), 1.40-2.46 (m, 10 H), 2.60 (dd, J=13.7, 6.3 Hz, 1H), 2.82-3.00 (m, 2H), 4.69 (s, 2H, —CH2OH), 5.04 (s, 2H, —CH2Ph), 6.28 (bs, 2H, —OH and NH), 6.73 (d, J=2.3 Hz, 1H), 6.80 (dd, J=8.6, 2.3 Hz, 1H), 7.21 (d, J=8.6 Hz, 1H), 7.30-7.45, (m, 5H). LRMS (FAB+): 91.1 (100), 415.3 (60, [M+H]+). HRMS (FAB+): 415.238434 C27H31N2O2 requires 415.238554

Workup

  1. customto destroy the excess of LiAlH4)
  2. stirringStirring
  3. waitwas continued for 1 hour
  4. addition(light yellowgreen suspension), acetic acid (0.5 mL) was added
  5. filtrationthe inorganic solids were filtered of and
  6. washwashed carefully with THF (ca. 50 mL).The combined organic layers
  7. dry with materialwere dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallised from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-846ab727bf5d4874b99c6ab5dc46bdaf
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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