Methanol → (2R,3R)-3-amino-4-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}butan-2-ol

HRID 1401833Notes

Reaction equation

[NH2:1][C@@H:2]([C@H:31]([OH:33])[CH3:32])[C:3]([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][CH:14]=[C:15]([C:17]3[CH:26]=[CH:25][C:24]4[C:23]([CH3:28])([CH3:27])[CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[C:19]=4[CH:18]=3)[N:16]=2)[CH2:8][CH2:7]1)=O.B.CO>C1COCC1>[NH2:1][C@H:2]([CH2:3][NH:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[S:13][CH:14]=[C:15]([C:17]3[CH:26]=[CH:25][C:24]4[C:23]([CH3:28])([CH3:27])[CH2:22][CH2:21][C:20]([CH3:29])([CH3:30])[C:19]=4[CH:18]=3)[N:16]=2)[CH2:10][CH2:11]1)[C@H:31]([OH:33])[CH3:32]

Participants

Conditions

Temperature: 70 °C

Procedure

115 mg (0.18 mmol) of (2S,3R)-2-amino-3-hydroxy-N-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-yl}butyramide was dissolved in 3 ml of THF, and 272 μl (0.54 mmol) of 2M borane dimethyl sufide solution in THF were added at 70° C. under nitrogen atmosphere, and the mixture was subsequently stirred at 70° C. for 2 hours. In order to decompose the excess borane, 1 ml of MeOH was added dropwise. The reaction mixture was evaporated, and 1 ml of water and 1 ml of conc HCl were added to the oily residue. The mixture was stirred at room temperature for 2 h, rendered alkaline using 2 molar NaOH and extracted with ethyl acetate. The organic phase was dried and purified by column chromatography on silica gel.

Workup

additionwas added dropwise
customThe reaction mixture was evaporated
addition1 ml of water and 1 ml of conc HCl were added to the oily residue
stirringThe mixture was stirred at room temperature for 2 h
extractionextracted with ethyl acetate
customThe organic phase was dried
custompurified by column chromatography on silica gel

Sources & evidence

ORD record: ord-a468a7d1563045ec92a72c29b9501c12
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907098B2

Reaction notes

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