1,1-Dichloroethane → (5-{2-[(Tetrahydro-pyran-4-ylmethyl)-amino]-ethyl}-thiazol-2-yl)-carbamic acid tert-butyl ester

HRID 1818931Notes

Reaction equation

HRID 1818931 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH2:15])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].[O:17]1[CH2:22][CH2:21][CH:20]([CH:23]=O)[CH2:19][CH2:18]1.ClC(Cl)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH:15][CH2:23][CH:20]2[CH2:21][CH2:22][O:17][CH2:18][CH2:19]2)=[CH:11][N:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 45117855tert-Butyl (5-(2-aminoethyl)thiazol-2-yl)carbamate

Product 1

HCID 86603170(5-{2-[(Tetrahydro-pyran-4-ylmethyl)-amino]-ethyl}-thiazol-2-yl)-carbamic acid tert-butyl ester

Procedure

A flask was charged with compound 14.1 (200 mg, 100 mol %), tetrahydro-pyran-4-carbaldehyde (100 mol %), and dichloroethane. To this was added NaBH(OAc)3 (150 mol %) and the resulting slurry was stirred at room temperature for 2 hours. The solvents were removed in vacuo and the residue was re-suspended in EtOAc and H2O. The organic layer was washed sequentially with saturated sodium bicarbonate, H2O, and brine. The organic layers were combined, dried over Na2SO4, and concentrated to give (5-{2-[(tetrahydro-pyran-4-ylmethyl)-amino]-ethyl}-thiazol-2-yl)-carbamic acid tert-butyl ester (compound 33.1) as an oil which was used in the next step without further purification.

Workup

  1. customThe solvents were removed in vacuo
  2. washThe organic layer was washed sequentially with saturated sodium bicarbonate, H2O, and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-994a4e451854454f83a7d6fcc8351638
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

Loading…