Hydrochloric Acid → methyl N-[2-(2,3-dihydro-1H-indol-4-yl)-2-hydroxyethyl]carbamate

HRID 255893

Reaction equation

HRID 255893 reaction equation
[B-][N+](C)(C)C.Cl.[NH:7]1[C:15]2[C:10](=[C:11]([CH:16]([OH:23])[CH2:17][NH:18][C:19](=[O:22])[O:20][CH3:21])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.O>O1CCOCC1>[NH:7]1[C:15]2[C:10](=[C:11]([CH:16]([OH:23])[CH2:17][NH:18][C:19](=[O:22])[O:20][CH3:21])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6327651Borane,N-dimethylmethanamine (1:1)HCID 13986141methyl N-[2-(1H-indole-4-yl)-2-hydroxyethyl]carbamate

Product 1

HCID 13986142methyl N-[2-(2,3-dihydro-1H-indol-4-yl)-2-hydroxyethyl]carbamateYield 98.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

35.5 g of borane-trimethylamine complex and then, slowly and while cooling to 10° C., 40.55 ml of 12N hydrochloric acid aqueous solution were added to a solution of 22.8 g of the product of Step A in 570 ml of dioxane and the mixture was stirred for 16 hours at ambient temperature. It was poured into 1,500 ml of water, washed with ethyl acetate, made alkaline with 48 ml of concentrated ammonia and was extracted with ethyl acetate. The organic phases were dried, filtered and evaporated to dryness to obtain 22.6 g of methyl N-[2-(2,3-dihydro-1H-indol-4-yl)-2-hydroxyethyl]carbamate which was crystallized from methanol to obtain 13.125 g of the product melting at ≃174° C.

Workup

  1. washwashed with ethyl acetate
  2. extractionwas extracted with ethyl acetate
  3. customThe organic phases were dried
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-33d42735a78644219418d993238233cb
Source dataset
uspto-grants-1987_10
Patent number
US04699907

Linked notes

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