Triethylamine → HCID 67513827, compound

HRID 1519542Notes

Reaction equation

HRID 1519542 reaction equation
[CH2:1]([N:4]([CH2:12][CH:13]=C)C(=O)OC(C)(C)C)[CH:2]=C.O=[O+][O-].[NH2:18][C@H:19]1[CH2:28][CH2:27][C:26]2[CH:25]=[C:24]([C:29]#[N:30])[CH:23]=[CH:22][C:21]=2[CH2:20]1.C(N(CC)CC)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[N:18]1([C@H:19]2[CH2:28][CH2:27][C:26]3[CH:25]=[C:24]([C:29]#[N:30])[CH:23]=[CH:22][C:21]=3[CH2:20]2)[CH2:13][CH2:12][NH:4][CH2:1][CH2:2]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 24823OzoneHCID 5049666Sodium triacetoxyborohydrideHCID 5107724tert-Butyl N,N-diallylcarbamateHCID 67514043HCID 67514043, compound

Product 1

HCID 67513827HCID 67513827, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl diallylcarbamate (0.63 g, 3.2 mmol) in DCM at −78° C. was bubbled ozone until a blue color persisted. Nitrogen was bubbled through the reaction to remove excess ozone, followed by addition of a DCM solution of (6S)-6-amino-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (0.14 g, 0.80 mmol) and triethylamine (0.22 mL, 1.6 mmol). Then NaB(OAc)3H (0.85 g, 4.0 mmol) was added to the reaction. The mixture was allowed to warm to RT and stir overnight. LC showed formation of the desired product, which was separated by prep-TLC to furnish 87 mg of tert-butyl 4-[(2S)-6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl]piperazine-1-carboxylate. LC-MS (IE, m/z): 173 [M+1]+. The material was further treated with TFA to afford crude (6S)-6-piperazin-1-yl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile.

Workup

  1. customNitrogen was bubbled through the reaction
  2. customto remove excess ozone

Sources & evidence

ORD record
ord-9f2175e20fbd4eb5889fe78d3415618d
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…