Lithium borohydride → HCID 58551033, compound

HRID 1908181Notes

Reaction equation

HRID 1908181 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3([C:32]4[CH:31]=[N:30][N:29]([CH3:33])[C:28]=4[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:21]3)[CH2:17][CH2:16]2)=[O:14])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1>[OH:8][CH2:7][C:6]1[CH:9]=[C:10]([C:13]([N:15]2[CH2:16][CH2:17][C:18]3([C:32]4[CH:31]=[N:30][N:29]([CH3:33])[C:28]=4[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:21]3)[CH2:19][CH2:20]2)=[O:14])[CH:11]=[CH:12][C:5]=1[O:4][CH:1]([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58551224HCID 58551224, compound

Product 1

HCID 58551033HCID 58551033, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Isopropoxy-5-(1-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carbonyl)benzaldehyde (110 mg, 0.25 mmol) was dissolved in THF (3 mL) and LiBH4 (11 mg, 0.50 mmol) was added. The reaction was stirred at room temperature for 1.5 h before being quenched with methanol (3 mL). The reaction was neutralized by the addition of a saturated sodium bicarbonate solution and was extracted with ethyl acetate (3×). The combined organic layers were dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane) to yield [3-(hydroxymethyl)-4-isopropoxy-phenyl]-(1-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (74 mg, 65%) as a white solid. ESI-MS m/z calc. 447.5. found 448.3 (M+1)+. Retention time: 1.59 minutes (3 min run).

Workup

  1. custombefore being quenched with methanol (3 mL)
  2. additionThe reaction was neutralized by the addition of a saturated sodium bicarbonate solution
  3. extractionwas extracted with ethyl acetate (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bb32d5c521684bed8608559ca4781b2a
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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