Methanol → HCID 23166911, compound

HRID 1087732Notes

Reaction equation

HRID 1087732 reaction equation
[OH:1][CH:2](/[CH:12]=[CH:13]/[C:14]1[C:15]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[N:18][N:17]2[C:26]=1[CH:27]([CH3:29])[CH3:28])[CH2:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].CO.[BH4-].[Na+]>O>[OH:11][CH:4]([CH2:3][CH:2]([OH:1])/[CH:12]=[CH:13]/[C:14]1[C:15]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[N:18][N:17]2[C:26]=1[CH:27]([CH3:29])[CH3:28])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86744243HCID 86744243, compound

Product 1

HCID 23166911HCID 23166911, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of ethyl (E)-5-hydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl) -3-oxohept-6-enoate [0.32 g; prepared as described in Reference Example 1(i)]in methanol (10 ml) under an atmosphere of argon was cooled to 0° C and treated with sodium borohydride (15.2 mg). The solution was stirred for 15 minutes and then it was poured into a mixture of ice and water (50 ml). The resulting mixture was extracted with diethyl ether (100 ml) and then with ethyl acetate (2×50 ml). The combined extracts were dried over magnesium sulphate, evaporated and subjected to flash chromatography on silica gel, using as eluant a mixture of petroleum ether (b.p. 40-60° C) and diethyl ether (1:1 v/v), to give ethyl (E)-3,5-dihydroxy-7-(3-isopropyl-1-phenylpyrrolo[2.1-a]phthalazin-2-yl)-hept -6-enoate (0.26 g) in the form of a yellow gum. [NMR (in a mixture of CDCl3 and D2O): 1.28 (3 H, t, J=7 Hz), 1.4-1.7 (2 H, m), 1.52 (6 H, d, J=7 Hz), 2.40-2.48 (2 H, m), 3.8 (1H, septet, J=7 Hz), 4.08-4.14 (3 H, m), 4.28-4.42 (1 H, m), 5.31 and 5.36 (1 H, two dd, J=16 Hz, 6 Hz), 6.63 and 6.65 (1 H, two dd, J=16 Hz, 1 Hz), 7.22-7.64 (9 H, m), 8.24 (1 H, s)].

Workup

  1. customprepared
  2. extractionThe resulting mixture was extracted with diethyl ether (100 ml)
  3. dry with materialThe combined extracts were dried over magnesium sulphate
  4. customevaporated
  5. additiona mixture of petroleum ether (b.p. 40-60° C) and diethyl ether (1:1 v/v)

Sources & evidence

ORD record
ord-00107d54c0d64b5993abbb01962bf707
Source dataset
uspto-grants-1990_10
Patent number
US04960775

Reaction notes

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