Tetrahydrofuran → Tert-butyl (2-{4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-1-yl}ethyl)carbamate

HRID 2090594Notes

Reaction equation

HRID 2090594 reaction equation
C1COCC1.Br.[CH3:7][C:8]1([CH3:31])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([C:20]3[N:21]=[C:22]([CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[S:23][CH:24]=3)[CH:11]=[CH:10][C:9]1=2.O=[CH:33][CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH3:7][C:8]1([CH3:31])[CH2:17][CH2:16][C:15]([CH3:18])([CH3:19])[C:14]2[CH:13]=[C:12]([C:20]3[N:21]=[C:22]([CH:25]4[CH2:30][CH2:29][N:28]([CH2:33][CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:27][CH2:26]4)[S:23][CH:24]=3)[CH:11]=[CH:10][C:9]1=2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 671662304-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrobromide

Product 1

HCID 44622055Tert-butyl (2-{4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-1-yl}ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10 ml of THF and 200 μl of glacial acetic acid are added to 200 mg (0.46 mmol) of 4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrobromide, and 154 mg (0.92 mmol) of tert-butyl (2-oxoethyl)carbamate are added. 195 mg (0.92 mmol) of sodium trisacetoxyborohydride are subsequently added, and the reaction mixture is stirred at room temperature for 24 h. The reaction mixture is filtered, the mother liquor is evaporated, and the residue is purified by preparative HPLC, giving “A37”;

Workup

  1. additionare added
  2. filtrationThe reaction mixture is filtered
  3. customthe mother liquor is evaporated
  4. customthe residue is purified by preparative HPLC
  5. customgiving “A37”

Sources & evidence

ORD record
ord-37b797f1a84645e5a0a733930b840122
Source dataset
uspto-grants-2013_05
Patent number
US08436186B2

Reaction notes

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