Dimethylformamide → (2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

HRID 2194940Notes

Reaction equation

HRID 2194940 reaction equation
[H-].[Na+].ClC([O:6][CH3:7])=O.[C:8](OCC)(=O)[CH3:9].[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C[N:21]([CH:23]=O)C>>[NH2:21][C:23]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:9]=1[CH2:8][C@H:7]([OH:6])[CH2:19][CH2:18]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexane

Product 1

HCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenolYield 73%

Procedure

Step-a product (13 g, 0.079 mol) was added portion wise to a mixture of 60% NaH (3 g, 0.09 mol, 1.25 eq) in DMF (52 ml) at 0° C. and stirred the contents for 1 hr at rt. Reaction contents were again cooled to 0° C., methyl chloroformate (11.19 g, 0.115 mol, 1.5 eq) was added drop wise for 30 min and the overall reaction mass was stirred for another 30 min. Progress of the reaction was monitored by TLC (30% ethyl acetate/hexane, Rf˜0.5). On completion of the reaction, ice cold water (300 ml) was added to the reaction contents. Solid thrown out was filtered and dried to yield the required product as a pale yellow colored solid (13 g, 73% yield).

Workup

  1. customReaction contents
  2. temperaturewere again cooled to 0° C.
  3. stirringthe overall reaction mass was stirred for another 30 min
  4. additionwas added to the reaction contents
  5. filtrationSolid thrown out was filtered
  6. customdried

Sources & evidence

ORD record
ord-c298324fc9b14481bad4b140c662c583
Source dataset
uspto-grants-2012_12
Patent number
US08334315B2

Reaction notes

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