Water → HCID 69054048, compound

HRID 2221358Notes

Reaction equation

HRID 2221358 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH:3]=O.[NH2:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][C:19]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH:16]=2)[O:11][C:10]([CH3:30])([CH3:29])[CH:9]1[OH:31].[BH3-]C#N.[Na+].O>CO>[CH2:22]([NH:21][C:19](=[O:20])[CH2:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([CH3:29])([CH3:30])[CH:9]([OH:31])[CH:8]2[NH:7][CH2:1][C:2]([CH3:6])([CH3:5])[CH3:3])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69063678HCID 69063678, compound

Product 1

HCID 69054048HCID 69054048, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

4 ml of trimethylacetaldehyde was added to a solution of 11 g of the 2-(4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-N-benzylacetamide obtained above in 200 ml methanol. 2.44 g of NaBH3CN was added in several portions, and the resulting suspension was stirred for 2 hours at 50° C. After cooling to room temperature, the reaction mixture was poured into 200 ml water. The aqueous phase was extracted once with 150 ml EA, the combined organic phases were dried over sodium sulfate, and the solvent was largely evaporated at reduced pressure. Chromatography of the remaining residue on silica gel (mobile phase: ethyl acetate/cyclohexane 1:1 v/v) and drying of the product fractions on a rotary evaporator yielded 10.8 g N-benzyl-2-[3-hydroxy-2,2-dimethyl-4-(neopentylamino)-3,4-dihydro-2H-chromen-6-yl]acetamide as colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous phase was extracted once with 150 ml EA
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customthe solvent was largely evaporated at reduced pressure
  5. customChromatography of the remaining residue on silica gel (mobile phase: ethyl acetate/cyclohexane 1:1 v/v) and drying of the product fractions on a rotary evaporator

Sources & evidence

ORD record
ord-303d56fd7a614e668829e1a2def02ad6
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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